DE1010739B - Process for the production of polysilicic acid esters of higher alcohols or phenols - Google Patents
Process for the production of polysilicic acid esters of higher alcohols or phenolsInfo
- Publication number
- DE1010739B DE1010739B DEK23950A DEK0023950A DE1010739B DE 1010739 B DE1010739 B DE 1010739B DE K23950 A DEK23950 A DE K23950A DE K0023950 A DEK0023950 A DE K0023950A DE 1010739 B DE1010739 B DE 1010739B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- phenols
- production
- higher alcohols
- polysilicic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001298 alcohols Chemical class 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title claims description 8
- 150000002989 phenols Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 description 10
- 239000000203 mixture Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JKGITWJSGDFJKO-UHFFFAOYSA-N ethoxy(trihydroxy)silane Chemical class CCO[Si](O)(O)O JKGITWJSGDFJKO-UHFFFAOYSA-N 0.000 description 1
- -1 ethyl silica Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical class CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/02—Polysilicates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Description
Verfahren zur Herstellung von Polykieselsäureestern höherer Alkohole oder Phenole Es ist bekannt, Kieselsäureester durch Einwirkung von Carbonsäuren zu Polyestern zu kondensieren. Die Kondensation vollzieht sich dabei unter Abspaltung eines Gemisches von Alkohol und Carbonsäureester. Das Verfahren führt bei Anwendung auf Methyl- und Äthylkieselsäureester zu Polyestern mit Molekulargewichten von. etwa 2000 bis 5000. Andererseits ist auch die Umesterung kondensierter Kiese.lsäure;eister niederer Alkohole mit höheren Alkoholen oder Phenolen bekannt.Process for the preparation of polysilicic acid esters of higher alcohols or phenols It is known to produce silicic acid esters by the action of carboxylic acids to condense to polyesters. The condensation takes place with splitting off a mixture of alcohol and carboxylic acid ester. The procedure leads when applied on methyl and ethyl silicic acid esters to polyesters with molecular weights of. about 2000 to 5000. On the other hand, the transesterification of condensed silicic acid is also an issue lower alcohols with higher alcohols or phenols known.
Um also zu solchen. Polyestern höherer Alkohcle oder Phenole zu kommen., war man, bisher darauf angewiesen, entweder zunächst einen. Polyester eines niederen Alkohols, z. B. Methyl- oder Äthylpolysilikat, herzustellen: und: diesen dann, in. einem zweiten Arbeitsgang mit einem höheren Alkohol umzu.estern, oder man hatte durch Umesterung von. Methyl- oder Äthyls.ilika:t zunächst einen monomeren Ester eines höheren Alkohols herzustellesi, dor dann ebenfalls in einem zweiten Arbeitsgang kondensiert werden mußte.So to such. Polyesters of higher alcohols or phenols., one was, until now dependent on it, either one at first. Polyester of a lower one Alcohol, e.g. B. methyl or ethyl polysilicate to produce: and: this then, in. a second operation with a higher alcohol, or one had by transesterification of. Methyl or ethyl silica: t initially a monomeric ester A higher alcohol can then also be produced in a second step had to be condensed.
Es wurde nun gefunden, daß man Polykieselsäureester höherer Alkohole oder Phenole in. eirein Arbeitsgang unter erheblichem Zeitgewinn aus den, leicht zugänglichen. Orthokieseilsäureestern der niederen Alkohole - vorzugsweise dies Meth.ano,ls und des Äthanols -- durch gleichzeitige, Umesterung mit einem höheren Alkohol oder e;inenn Phenol und Kondensation mit Carbonsäuren in der Hitze herstellen kann.. Die Kondensation wird vorzugsweise durch Zugabe von wasserfreie-r Ameisensäure bewirkt. Durch Variieren der zugesetzten Mengen der Carbon.säure und des höheren, Alkohols oder Phenols können verschieden substituierte und verschieden hoch. kondensierte Polykieselsäureester erhalten werden, die flüssig,. viskos oder hart sind und gute Löslichkeit besitzen.It has now been found that polysilicic acid esters of higher alcohols can be used or phenols in one operation with considerable time savings from the, easily accessible. Orthosilicic acid esters of the lower alcohols - preferably this Meth.ano, ls and ethanol - by simultaneous, transesterification with a higher Alcohol or phenol and condensation with carboxylic acids produce in the heat can .. The condensation is preferably carried out by adding anhydrous formic acid causes. By varying the added amounts of carboxylic acid and the higher, Alcohol or phenol can have different substituents and different levels. condensed Polysilicic acid esters are obtained which are liquid. viscous or hard and good Have solubility.
Die erhaltenen Polyester können als Lackkunstharze, insbesondere für hochhitzebeständige Anstriche, verwendet werden. Beispiel 1 1 Mol Orthoki;eiselsäureäthylester wird mit einean Gemisch von 2 Mol Cyclohexanol, 1 Mol Essigsäure und Iho Mol Acetylchlo-rid unter einer Kolonne 5 Stunden auf 160° erhitzt. Das entstehende Äthyla,cetat-Alkohol-Gemisch wird während der Reaktion. fortlaufend über die Kolonnen abdestilliert. Anschließend werden die leichtsiedenden Anteile im Vakuum bis zu einer Badtemperatur von. 310° entfernt. Man erhält einen hochviskosen Polyester mit 31% Si O., und einem Molekulargewicht von etwa 1300. Beispiel 2 1 Mol Orthokieselsäureäthylester wird mit 1,1 Mol Methylcyclohexanol und mit 1,4 Mol Ameisensäure (wasserfrei) gemischt und unter einer Kolonne 4 St.un,-den auf 80 bis 145° erhitzt. Das entstehende Gemisch von. Alkohol und Äthv1formiat wird über die Kolonne abdestilliert. Dann, wird ein Vakuum von etwa 1 mm angelegt. Nach einer weiteren Stunde, wobei die Temperatur bis auf etwa, 300° steigt, werden das überschüssige Methylcyclohexa.ilol und niedrigsiedende Oligokieselsäure-Mischester des Äthanols un.d Methy 1-cyclohexanols entfernt. Man erhält einen in der Hitze viskosen. Polyester, der nach dem Abkühlen hart und nicht mehr schmelzbar ist. Dieses Hartharz ist farl>-los; es ist in. Testbenzin löslich. Der Gehalt an SiO2 beträgt etwa 45%, das Molekularge;wic:ht etwa. 3900. Beispiel 3 1 Mol Orthokieselsäureäthylester wird mit 1,1 Mod 2-Äthyl-hexanol und mit 1,4 Mol Ameisensäure gemischt und unter einer Kolonne 4 Stunden auf 75 bis 140° erhitzt. Das entstehende Gemisch von. Alkohol und Äthylfo,rmiat wird über die Kolonne abdestilliert. Dann wird. ein Vakuum von etwa, 1 mm angelegt. Nach einer weiteren Stunde, wobei die Temperatur bis auf etwa 380° steigt, werden das überschüssige 2-Äthyl-hexa:n,od und niedrigsiedende OligokieiseIsäure-Mischester des Äthanols und 2-Äthyl-hexaiio-ls eintfernt. Man erhält einen Polyester von niedriger Viskosität. Der Polyester ist farblos und in. Lösungsmitteln, löslich. Der Gehalt an Si 02 beträgt etwa 40 °/o. das Molekulargewicht etwa 3100.The polyesters obtained can be used as synthetic resins, especially for highly heat-resistant paints can be used. Example 1 1 mol of Orthoki; ethyl acetate is with a mixture of 2 moles of cyclohexanol, 1 mole of acetic acid and 1 mole of acetyl chloride heated under a column to 160 ° for 5 hours. The resulting ethyl acetate-alcohol mixture will during the reaction. continuously distilled off over the columns. Afterward are the low-boiling components in a vacuum up to a bath temperature of. 310 ° removed. A highly viscous polyester with 31% Si O. and a molecular weight is obtained of about 1300. Example 2 1 mol of ethyl orthosilicate is mixed with 1.1 mol of methylcyclohexanol and mixed with 1.4 mol of formic acid (anhydrous) and under a column 4 hours, -den heated to 80 to 145 °. The resulting mixture of. Alcohol and Ethyl formate distilled off over the column. Then, a vacuum of about 1 mm is applied. To Another hour, with the temperature rising to around .300 °, that will be excess methylcyclohexa.ilol and low-boiling oligosilicic acid mixed esters of the ethanol and methyl 1-cyclohexanol removed. You get one in the heat viscous. Polyester, which after cooling is hard and no longer meltable. This Hard resin is farl> -less; it is soluble in white spirit. The SiO2 content is about 45%, the molecular weight is about. 3900. Example 3 1 mol of ethyl orthosilicate is mixed with 1.1 Mod 2-ethyl-hexanol and with 1.4 mol of formic acid and under a column heated to 75 to 140 ° for 4 hours. The resulting mixture of. alcohol and Ethylfo, rmiat is distilled off over the column. Then it will be. a vacuum of about, 1 mm applied. After another hour, the temperature is down to about 380 ° rises, the excess 2-ethyl-hexa: n, od and low-boiling oligo-icing acid mixed esters of the ethanol and 2-ethyl-hexaiio-ls. You get one Low viscosity polyester. The polyester is colorless and in. Solvents, soluble. The Si 02 content is about 40%. the molecular weight about 3100.
_ Beispiel-4 1 Mol Orthokieselsäureäthylester wird mit 1,1 Mol Phenol und mit 1,4 Mol Ameisensäure gemischt und unter einer Kolonne 4 Stunden auf 90 bis 150° erhitzt. Das entstehende azeotrope Gemisch von Alkohol und Äthylformiat wird über die Kolonne abdestilliert. Dann. wird unterVakuum weiterdestilliert. Nach einer weiteren Stunde, wobei die Temperatur bis auf etwa 250° steigt, werden, das überschüssige Phenol und niedrigsiedende OligokieselsäureMischester des Äthanols und Phenols entfernt. Man erhält einen Polyester, der ein hochviskoses Weichharz von schwachgelber Farbe darstellt. Das Weichharz ist in Xylol löslich. Der Gehalt an Si 02 beträgt etwa 52%, das Mojekulargewicht beträgt etwa 2500._ Example-4 1 mol of orthosilicic acid ethyl ester is mixed with 1.1 mol of phenol and mixed with 1.4 mol of formic acid and under a column for 4 hours to 90 to 150 ° heated. The resulting azeotropic mixture of alcohol and ethyl formate is distilled off over the column. Then. is further distilled under vacuum. After a another hour, with the temperature rising to about 250 °, the excess Phenol and low-boiling oligosilicic acid mixed esters of ethanol and phenol removed. A polyester is obtained which is a highly viscous soft resin of pale yellow color represents. The soft resin is soluble in xylene. The Si 02 content is approximately 52%, the mojecular weight is about 2500.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK23950A DE1010739B (en) | 1954-11-03 | 1954-11-03 | Process for the production of polysilicic acid esters of higher alcohols or phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK23950A DE1010739B (en) | 1954-11-03 | 1954-11-03 | Process for the production of polysilicic acid esters of higher alcohols or phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1010739B true DE1010739B (en) | 1957-06-19 |
Family
ID=7216884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK23950A Pending DE1010739B (en) | 1954-11-03 | 1954-11-03 | Process for the production of polysilicic acid esters of higher alcohols or phenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1010739B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191968B (en) | 1958-04-05 | 1965-04-29 | Siemens Ag | Process for the production of linear polymeric silicic acid mixed esters |
| EP3199570A1 (en) | 2016-01-26 | 2017-08-02 | Evonik Degussa GmbH | Method for producing a composition containing 2-ethyl hexylsilicate |
| EP3231807A1 (en) | 2016-04-12 | 2017-10-18 | Evonik Degussa GmbH | Method for producing a composition containing 2-prophyleptyl silicate |
| EP3315496A1 (en) | 2016-10-25 | 2018-05-02 | Evonik Degussa GmbH | 3-glycidyloxypropyltrialkoxysilanes with long-chain alkoxy groups, method for preparation and use |
| EP3351547A1 (en) | 2017-01-23 | 2018-07-25 | Evonik Degussa GmbH | Method for producing a composition containing 2-ethyl hexylsilicate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2490691A (en) * | 1946-10-03 | 1949-12-06 | Du Pont | Alkyl polysilicates |
| FR1008820A (en) * | 1949-01-25 | 1952-05-22 | Pierce John B Foundation | Compositions used in particular for high temperature lubrication, sealing and deep vacuum lubrication, heat transmission, etc. and processes for their preparation |
| GB706029A (en) * | 1950-01-06 | 1954-03-24 | California Research Corp | Mixtures of alkoxysiloxanes |
-
1954
- 1954-11-03 DE DEK23950A patent/DE1010739B/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2490691A (en) * | 1946-10-03 | 1949-12-06 | Du Pont | Alkyl polysilicates |
| FR1008820A (en) * | 1949-01-25 | 1952-05-22 | Pierce John B Foundation | Compositions used in particular for high temperature lubrication, sealing and deep vacuum lubrication, heat transmission, etc. and processes for their preparation |
| GB706029A (en) * | 1950-01-06 | 1954-03-24 | California Research Corp | Mixtures of alkoxysiloxanes |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191968B (en) | 1958-04-05 | 1965-04-29 | Siemens Ag | Process for the production of linear polymeric silicic acid mixed esters |
| EP3199570A1 (en) | 2016-01-26 | 2017-08-02 | Evonik Degussa GmbH | Method for producing a composition containing 2-ethyl hexylsilicate |
| EP3231807A1 (en) | 2016-04-12 | 2017-10-18 | Evonik Degussa GmbH | Method for producing a composition containing 2-prophyleptyl silicate |
| EP3315496A1 (en) | 2016-10-25 | 2018-05-02 | Evonik Degussa GmbH | 3-glycidyloxypropyltrialkoxysilanes with long-chain alkoxy groups, method for preparation and use |
| EP3351547A1 (en) | 2017-01-23 | 2018-07-25 | Evonik Degussa GmbH | Method for producing a composition containing 2-ethyl hexylsilicate |
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